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Manganese(II) complexes of biological relevance: Synthesis and spectroscopic characterization of novel manganese(II) complexes with monobasic bidentate ligands derived from halo-substituted 1H-indole-2,3-diones

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Abstract

Novel biologically significant manganese(II) complexes with four monobasic bidentate ligands L1H [2-(5-fluoro-2-dihydro-2-oxo-1H-indol-3-ylidene)hydrazinecarboxamide], L2H [2-(5-fluoro-2-dihydro-2-oxo-1H-indol-3-ylidene)hydrazinecarbothioamide], L3H [2-(5-bromo-2-dihydro-2-oxo-1H-indol-3-ylidene)hydrazinecarboxamide] and L4H [2-(5-bromo-2-dihydro-2-oxo-1H-indol-3-ylidene)hydrazinecarbothioamide] were synthesized by complexation of the ligands with MnCl2·4H2O in 1: 1 and 1: 2 molar ratios in methanol. The Schiff base ligands and complexes were characterized by elemental analyses, melting points, molecular weights, IR, 1H and 13C NMR, UV–Vis, EPR, and mass spectra, as well as X-ray powder diffraction patterns. Based on the spectral data, a tetrahedral geometry was proposed for all the synthesized metal complexes. The ligands and complexes were tested in vitro against bacteria (Escherichia coli and Staphylococcus aureus) and fungi (Fusarium semitectum and Aspergillus flavus) to show that they were active against all the microbial strains examined, and the metal complexes were more active in comparison with the ligands. DNA cleavage activity of the complexes was examined by gel electrophoresis.

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References

  1. Fahmi, N. and Singh, R.V., Transition Met. Chem., 1994, vol. 19, p. 453. doi 10.1007/BF0a0139327

    CAS  Google Scholar 

  2. Türkkan, B., Sariboga, B., and Sariboga, N., Transition Met. Chem., 2011, vol. 36, p. 679. doi 10.1007/s11243- 011-9518-7

    Article  Google Scholar 

  3. Singh, K., Barwa, M. S., and Tyagi, P., Eur. J. Med. Chem., 2006, vol. 41, p. 147. doi 10.1016/j.ejmech.2005.06.006

    Article  Google Scholar 

  4. Majumder, A., Rosair, G. M., Mallick, A., Chattopadhyay, N., and Mitra, S., Polyhedron, 2006, vol. 25, p. 1753. doi 10.1016/j.poly.2005.11.029

    Article  CAS  Google Scholar 

  5. Freiria, A., Bastida, R., Valencia, L., Macias, A., and Lodeiro, C., Inorg. Chim. Acta., 2006 vol. 359, p. 2383. doi 10.1016/j.ica.2005.12.055

  6. Chohan, Z.H., Rauf, A., and Supuran, C.T., Met. Based Drugs, 2001, vol. 8, p. 287. doi 10.1155/MBD.2002.287

    Article  CAS  Google Scholar 

  7. Osowale, A., Kolawale, G.A., and Fagade, O.E., J. Coord. Chem., 2008, vol. 67, p. 1046. doi 10.1080/00958970701482446

    Article  Google Scholar 

  8. Shamsipur, M., Yousefi, M., Hosseini, M., Ganjali, M., Sharghi, H., and Naeimi, H.A., Anal. Chem., 2001, vol. 73, p. 2869. doi 10.1021/ac001449d

    Article  CAS  Google Scholar 

  9. Genin, J.M., Biles, C., Keiser, J.B., Poppe, S.M, Swaney, S.M., Tarpley, W.G., Romero, D.L., and Yage, Y.., J. Med. Chem., 2000, vol. 43, p. 1034. doi 10.1021/jm990383f

    Article  CAS  Google Scholar 

  10. Nishat, N., Khan, S. A., Parveen, S., and Rasool, R., J. Coord. Chem., 2010, vol. 63, p. 3944. doi 10.1080/00958972.2010.526207

    Article  CAS  Google Scholar 

  11. Somogyi, L., Bull. Chem. Soc. Jpn., 2001, vol. 74, p. 873. doi 10.1246/bcsj.74.873

    Article  CAS  Google Scholar 

  12. Nejo, A.A., Kolawole, G.A., Dumbele, M.C., and Opoku, A.R., J. Coord. Chem., 2010, vol. 63, p. 4367. doi 10.1080/00958972.2010.539684

    Article  CAS  Google Scholar 

  13. Yang, M., Zhang, Y.H., Li, M.X., Lu, Y.L., and Zhang, N., J. Coord. Chem., 2013, vol. 66, p. 3327. doi 10.1080/00958972.2013.834333

    Article  CAS  Google Scholar 

  14. Bal, T. R., Anand, B., Yogeeswari, P., and Sriram, D., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 4451. doi 10.1016/j.bmcl.2005.07.046

    Article  CAS  Google Scholar 

  15. Pandeya, S.N. and Sriram, D., Acta. Pharm. Turc., 1998, vol. 40, p. 33.

    CAS  Google Scholar 

  16. Bacchi, A., Carcelli, M., Pelagatti, P., Pelizzi, G., Rodriguez Arguelles, M.C., Rogolino, D., Solinas, C., and Zani, F., J. Inorg. Biochem., 2005, vol. 99, p. 397. doi 10.1016/j.jinorgbio.2004.10.008

    Article  CAS  Google Scholar 

  17. Cerchiaro, G., Aquilano, K., Filomeni, G., Rotilio, G., Ciriolo, M.R., and Ferriera, A.M.D.C., J. Inorg. Biochem., 2005, vol. 99 p. 1433. doi 10.1016/j.jinorgbio.2005.03.013

    Article  CAS  Google Scholar 

  18. Verma, M., Pandeya, S.N., Singh, K.N., and Stables, J.P., Acta. Pharm., 2004, vol. 54, p. 49.

    CAS  PubMed  Google Scholar 

  19. Jarrahpour, A., Khalili, D., Clercq, E D., Salmi, C., and Brunel, J.M., Molecules, 2007, vol. 12, p. 1720. doi 10.3390/12081720

    Article  CAS  Google Scholar 

  20. Rainsford, K.D. and Whitehouse, M.W., J. Pharm. Pharmacol., 1976, vol. 28, p. 83. doi 10.1111/j.2042- 7158.1976.tb04035.x

    Article  CAS  Google Scholar 

  21. Ferrari, M.B., Capacchi, S., Bisceglie, F., Pelosi, G., and Tarasconi, P., Inorg. Chim. Acta., 2001, vol. 312, p. 81. doi 10.1016/S0020-1693(00)00339-X

    Article  CAS  Google Scholar 

  22. Singh, L., Mohan, G., Prashar, R. K., Tripathi, S.P., and Sharma, R.C., Curr. Sci., 1986, vol. 55, p. 846.

    CAS  Google Scholar 

  23. Elsome, A.M., Hamilton-Miller, J.M.T., Brumfitt, W., and Noble, W.C., J. Antimicrob. Chemother., 1996, vol. 37, p. 911. doi 10.1093/jac/37.5.911

    Article  CAS  Google Scholar 

  24. Badwaik, V.B., Deshmukh, R.D., and Aswar, A.S., J. Coord. Chem., 2009, vol. 62, p. 2037. doi 10.1080/00958970902741244

    Article  CAS  Google Scholar 

  25. Li, Y., Wu, Y., Zhao, J., and Yang, P., J. Inorg. Biochem. 2007 vol. 101, p. 283. doi 10.1016/j.jinorgbio.2006.10.004

  26. Zhang, N., Fan, Y.H., Bi, C.F., Zuo, J., Zhang, P.F., Zhang, Z.Y., and Zhu, Z., J. Coord. Chem., 2013, vol. 66, p. 1933. doi 10.1080/00958972.2013.796039

    Article  CAS  Google Scholar 

  27. Wang, X.L., Chao, H., Hong, L., Hong, X.L., Nian, Ji.L., and Yuan, Li.X., J. Inorg. Biochem., 2004, vol. 98, p. 423. doi 10.1016/j.jinorgbio.2003.12.006

    Article  CAS  Google Scholar 

  28. Patil, S.A, Naik, V.H., Kumar, A., Kulkarni, D., Kamble, U.K., Bagihalli, G.B., and Badami, P.S., J. Coord. Chem., 2010, vol. 63, p. 688. doi 10.1016/j.jinorgbio.2003.12.006

    Article  CAS  Google Scholar 

  29. Raman, N., Jeyamurugan, R., Rani, R.U., Baskaran, T., and Mitu, L., J. Coord. Chem., 2010, vol. 63, p. 1629. doi 10.1080/00958972.2010.485643

    Article  CAS  Google Scholar 

  30. Bagihalli, G.B. and Patil, S.A., J. Coord. Chem., 2009, vol. 62, p. 1690. doi 10.1080/00958970802668851

    Article  CAS  Google Scholar 

  31. Barve, V., Ahmed, F., Adsule, S., and Banerjee, S., J. Med. Chem., 2006, vol. 49, p. 3800. doi 10.1021/jm051068y

    Article  CAS  Google Scholar 

  32. Saglam, N., Colak, A., Serbest, K., Dülger, S., Güner, S., Karaböcek, S., and Beldüz, A.O., Bio. Metals., 2002, vol. 15, p. 357. doi 10.1023/A:1020228723299

    CAS  Google Scholar 

  33. Refat, M.S., El-Deen, I.M., Anwer, Z.M., and El-Ghol, S., J. Coord. Chem., 2009, vol. 62, p. 1709. doi 10.1080/00958970802684205

    Article  CAS  Google Scholar 

  34. Gupta, K.C. and Sutar, A.K., Coord Chem Rev., 2008, vol. 252, p. 1420. doi 10.1016/j.ccr.2007.09.005

    Article  CAS  Google Scholar 

  35. Zhou, Y. and Peng, J.N., J. Coord. Chem., 2013, vol. 15, p. 2597. doi 10.1080/00958972.2013.811495

    Article  Google Scholar 

  36. Cozzi, P.G., Chem. Soc. Rev., 2004, vol. 33, p. 410. doi 10.1039/B307853C

    Article  CAS  Google Scholar 

  37. Fahmi, N., Sharma, D.K., and Singh, R.V., Synth. React. Inorg. Met. Org. Chem., 1994, vol. 24, p. 377. doi 10.1080/00945719408000118

    Article  CAS  Google Scholar 

  38. Joseph, J. and Mehta, B.H. Russ. J. Coord. Chem., 2007, vol. 33, p. 124. doi 10.1134/S1070328407020091

  39. Saxena, C., Bhardwaj, N. C., Singh, D., and Singh, R.V., Synth. React. Inorg. Met. Org. Chem., 1993, vol. 23, p. 1391. doi 10.1080/15533179308016694

    Article  CAS  Google Scholar 

  40. Raman, N., Thalamuthu, S., Raja, J.D., Neelakandan, M.A., and Banerjee, S., J. Chil. Chem. Soc., 2008, vol. 53(1), p. 1450. doi 10.4067/S0717-97072008000100025

    CAS  Google Scholar 

  41. Sampath, K. and Jayabalakrishnan, C., J. Environ. Nanotechnol., 2013, vol. 2(4), p. 34. doi 10.13074/jent.2013.12.132043

    Article  Google Scholar 

  42. Vogel, A.I., A Textbook of Organic Quantitative Analysis, London, 2004, 5th ed.

    Google Scholar 

  43. Makode, J.T. and Aswar, A.S., Indian J. Chem., 2004, vol. 43A, p. 2120. http://nopr.niscair.res.in/handle/123456789/20435.

    CAS  Google Scholar 

  44. Vogel, A.I., A Textbook of Quantitative Chemical Analysis, London, 2006, 6th ed.

    Google Scholar 

  45. Zahid, H., Chohan, M., and Arif, M.S., Appl. Organomet. Chem., 2007, vol. 21, p. 294. doi 10.1002/aoc.1200

    Article  Google Scholar 

  46. Raman, N., Raja, J. D., Sakthivel, A., J. Chem. Sci., 2007, vol. 119, p. 303. doi 10.1007/s12039-007-0041-5

    Article  CAS  Google Scholar 

  47. Arish, D. and Nair, M.S., J. Coord. Chem., 2010, vol. 63, p. 1619. doi 10.1080/00958972.2010.483729

    Article  CAS  Google Scholar 

  48. Kapoor, P., Singh, R.V., and Fahmi, N., J. Coord. Chem., 2012, vol. 65(2), p. 262. doi 10.1080/00958972.2011.649265

    Article  CAS  Google Scholar 

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Sharma, S., Meena, R., Satyawana, Y. et al. Manganese(II) complexes of biological relevance: Synthesis and spectroscopic characterization of novel manganese(II) complexes with monobasic bidentate ligands derived from halo-substituted 1H-indole-2,3-diones. Russ J Gen Chem 86, 2807–2816 (2016). https://doi.org/10.1134/S1070363216120446

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